Crossborder tax filing is an annual challenge, which is why I attended yesterday’s How to Survive Tax Day as an American Abroad 2025 webinar by the Democrats Abroad Taxation Task Force. It was packed with valuable information, and if you’re navigating the US expat filing tax maze, I highly recommend checking it out.

Here are a few things that stood out for me:

1. DIY Accuracy vs. Accountant “Audit Insurance”

One point that really resonated was the discussion around tax preparation accuracy. The webinar highlighted something crucial: hiring an accountant isn’t necessarily “audit insurance,” and accuracy can often be higher when you prepare your own return. This mirrors my own experience — while I was always confident filing my own taxes stateside, I’ve used accountants for both our US and Canadian returns since moving north and I do the prep alongside them as a learning exercise, with the goal of eventually taking it back to DIY. Over the years, I’ve caught errors in the accountant-prepared versions more than once. This isn’t intended as a criticism — it’s the nature of the game — but it underscores that nobody cares about your return’s accuracy as much as you do. Hearing this perspective might just be the nudge I need to take the reins fully next tax season.

2. The Hidden Costs of Tax Software

Another eye-opening segment focused on the practices of major tax software companies like TurboTax and H&R Block. I’ll admit, I’ve used them in the past without much thought. However, the webinar pointed out that these companies spend millions lobbying Congress against simplifying the tax code and blocking free filing initiatives. While perhaps not shocking in hindsight, it hadn’t explicitly occurred to me before. Their business model thrives on complexity and obfuscation. If and when I return to full DIY filing, I’ll actively avoid these platforms. Based on what I’ve learned, I’ll likely use myexpattaxes for my US return, and Wealthsimple for on the Canadian side.

3. Tax Advocacy for Americans Abroad

Finally, the webinar reinforced the value of the work being done by the DA’s Taxation Task Force. They are actively advocating for significant changes that would simplify life for US expats, pushing Congress on critical issues like:

• Residency-Based Taxation (RBT): Taxing based on where you live, not your citizenship.
• FATCA Relief: Easing the burdensome Foreign Account Tax Compliance Act requirements for ordinary citizens abroad.
• Simplification Initiatives: Generally making the crossborder tax process less painful.

It was encouraging to hear that a bill for residency-based taxation (H.R. 10468) was introduced in December 2024. It’s currently undergoing scoring to assess its fiscal impact – a necessary step before it can potentially advance. It’s a long road, but seeing concrete legislative efforts is a positive sign. Supporting organizations like the DA Taxation Task Force feels like a direct way to contribute to making our crossborder financial lives easier.

Final Thoughts

Overall, I left the session feeling better equipped and more confident about navigating the US tax system from Canada. If this sounds relevant to you, I definitely encourage you to watch the webinar.

You can check out the rest of their 2025 webinar series here. They have one coming up on May 21 on filing the FBAR.